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Showing metabocard for trans-4-Hydroxycyclohexylacetic acid (HMDB0000909)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:17 UTC
HMDB IDHMDB0000909
Secondary Accession Numbers
  • HMDB00909
Metabolite Identification
Common Nametrans-4-Hydroxycyclohexylacetic acid
Descriptiontrans-4-Hydroxycyclohexylacetic acid, also known as 4-hydroxycyclohexyl acetate, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. trans-4-Hydroxycyclohexylacetic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make trans-4-hydroxycyclohexylacetic acid a potential biomarker for the consumption of these foods. trans-4-Hydroxycyclohexylacetic acid, with regard to humans, has been linked to the inborn metabolic disorder hawkinsinuria. Based on a literature review a small amount of articles have been published on trans-4-Hydroxycyclohexylacetic acid.
Structure
Data?1676999717
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000909 (trans-4-Hydroxycyclohexylacetic acid)

trans-2-Octenoic acid.mol
  Mrv0541 02231218492D          

 11 11  0  0  0  0            999 V2000
    0.0000   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  1  8  1  1  0  0  0
  4 11  1  6  0  0  0
M  END
Download

3D MOL for HMDB0000909 (trans-4-Hydroxycyclohexylacetic acid)

HMDB0000909
     RDKit          3D
trans-4-Hydroxycyclohexylacetic acid
 25 25  0  0  0  0  0  0  0  0999 V2000
    3.6603    1.3421   -0.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001    0.3413   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057   -0.3932    0.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7592   -0.0123   -1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5092    0.4169   -0.4779 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6750   -0.0064   -1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8870   -0.4061   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0389    0.1381    0.8272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9425    1.2243    0.8686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002    0.5555    1.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -0.2075    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1047   -0.0320    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186    0.5117   -2.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -1.0949   -1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    1.5091   -0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705    0.7981   -2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516   -0.8923   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7766   -0.0579   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0116   -1.5299   -0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303   -0.6469    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742    0.8731    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5907    1.6435    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7792    0.3432    2.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230   -0.0913    1.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -1.2358    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  1
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  1
  9 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
M  END
Download

3D SDF for HMDB0000909 (trans-4-Hydroxycyclohexylacetic acid)

trans-2-Octenoic acid.mol
  Mrv0541 02231218492D          

 11 11  0  0  0  0            999 V2000
    0.0000   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  1  8  1  1  0  0  0
  4 11  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000909

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1CC[C@H](CC(O)=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)/t6-,7-

> <INCHI_KEY>
ALTAAUJNHYWOGS-LJGSYFOKSA-N

> <FORMULA>
C8H14O3

> <MOLECULAR_WEIGHT>
158.195

> <EXACT_MASS>
158.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.847451949929287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1r,4r)-4-hydroxycyclohexyl]acetic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.6920394593333334

> <ALOGPS_LOGS>
-0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.082507897763794

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.649244089672353

> <JCHEM_PKA_STRONGEST_BASIC>
-1.450511452986881

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
40.0905

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1r,4r)-4-hydroxycyclohexyl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000909 (trans-4-Hydroxycyclohexylacetic acid)

HMDB0000909
     RDKit          3D
trans-4-Hydroxycyclohexylacetic acid
 25 25  0  0  0  0  0  0  0  0999 V2000
    3.6603    1.3421   -0.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001    0.3413   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057   -0.3932    0.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7592   -0.0123   -1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5092    0.4169   -0.4779 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6750   -0.0064   -1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8870   -0.4061   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0389    0.1381    0.8272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9425    1.2243    0.8686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002    0.5555    1.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -0.2075    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1047   -0.0320    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186    0.5117   -2.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -1.0949   -1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    1.5091   -0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705    0.7981   -2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516   -0.8923   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7766   -0.0579   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0116   -1.5299   -0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303   -0.6469    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742    0.8731    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5907    1.6435    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7792    0.3432    2.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230   -0.0913    1.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -1.2358    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  1
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  1
  9 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
M  END
Download

PDB for HMDB0000909 (trans-4-Hydroxycyclohexylacetic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: trans-2-Octenoic acid.mol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.001   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    8    9   10                                                  
CONECT    8    7    1                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    4                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0000909 (trans-4-Hydroxycyclohexylacetic acid)

COMPND    HMDB0000909
HETATM    1  O1  UNL     1       3.660   1.342  -0.873  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.000   0.341  -0.511  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.506  -0.393   0.550  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.759  -0.012  -1.190  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.509   0.417  -0.478  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.675  -0.006  -1.291  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.887  -0.406  -0.529  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.039   0.138   0.827  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.942   1.224   0.869  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.800   0.556   1.529  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.356  -0.208   0.883  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.105  -0.032   1.248  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.719   0.512  -2.195  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.777  -1.095  -1.452  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.515   1.509  -0.394  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.870   0.798  -2.054  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.352  -0.892  -1.906  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.777  -0.058  -1.135  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.012  -1.530  -0.545  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.530  -0.647   1.462  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.874   0.873   0.893  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.591   1.643   1.380  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.779   0.343   2.600  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.223  -0.091   1.550  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.001  -1.236   0.763  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   11   15
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9   10   20
CONECT    9   21
CONECT   10   11   22   23
CONECT   11   24   25
END
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SMILES for HMDB0000909 (trans-4-Hydroxycyclohexylacetic acid)

O[C@H]1CC[C@H](CC(O)=O)CC1
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INCHI for HMDB0000909 (trans-4-Hydroxycyclohexylacetic acid)

InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)/t6-,7-
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View in JSmolView Stereo Labels
Synonyms
ValueSource
trans-4-HydroxycyclohexylacetateGenerator
4-Hydroxy-cyclohexyl acetic acid esterHMDB
4-Hydroxycyclohexyl acetateHMDB
2-[(1R,4R)-4-Hydroxycyclohexyl]acetateHMDB
Chemical FormulaC8H14O3
Average Molecular Weight158.195
Monoisotopic Molecular Weight158.094294314
IUPAC Name2-[(1r,4r)-4-hydroxycyclohexyl]acetic acid
Traditional Name[(1r,4r)-4-hydroxycyclohexyl]acetic acid
CAS Registry Number68592-23-4
SMILES
O[C@H]1CC[C@H](CC(O)=O)CC1
InChI Identifier
InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)/t6-,7-
InChI KeyALTAAUJNHYWOGS-LJGSYFOKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Cyclic alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility27.1 g/LALOGPS
logP0.93ALOGPS
logP0.69ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.09 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.37831661259
DarkChem[M-H]-129.52231661259
AllCCS[M+H]+136.35632859911
AllCCS[M-H]-135.72732859911
DeepCCS[M+H]+134.90830932474
DeepCCS[M-H]-132.51230932474
DeepCCS[M-2H]-167.81430932474
DeepCCS[M+Na]+142.27330932474
AllCCS[M+H]+136.432859911
AllCCS[M+H-H2O]+132.132859911
AllCCS[M+NH4]+140.332859911
AllCCS[M+Na]+141.532859911
AllCCS[M-H]-135.732859911
AllCCS[M+Na-2H]-137.232859911
AllCCS[M+HCOO]-138.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.10.13 minutes32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.09 minutes32390414
Predicted by Siyang on May 30, 20229.5042 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.7 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid195.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1312.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid273.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid106.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid171.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid187.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid308.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid330.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)179.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid700.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid268.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid982.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid191.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid244.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate668.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA278.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water297.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-4-Hydroxycyclohexylacetic acidO[C@H]1CC[C@H](CC(O)=O)CC12625.2Standard polar33892256
trans-4-Hydroxycyclohexylacetic acidO[C@H]1CC[C@H](CC(O)=O)CC11420.4Standard non polar33892256
trans-4-Hydroxycyclohexylacetic acidO[C@H]1CC[C@H](CC(O)=O)CC11473.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-4-Hydroxycyclohexylacetic acid,1TMS,isomer #1C[Si](C)(C)O[C@H]1CC[C@H](CC(=O)O)CC11514.7Semi standard non polar33892256
trans-4-Hydroxycyclohexylacetic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C[C@H]1CC[C@H](O)CC11521.4Semi standard non polar33892256
trans-4-Hydroxycyclohexylacetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C[C@H]1CC[C@H](O[Si](C)(C)C)CC11576.7Semi standard non polar33892256
trans-4-Hydroxycyclohexylacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H](CC(=O)O)CC11785.8Semi standard non polar33892256
trans-4-Hydroxycyclohexylacetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@H]1CC[C@H](O)CC11766.1Semi standard non polar33892256
trans-4-Hydroxycyclohexylacetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC12045.8Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableHawkinsinuria details
Associated Disorders and Diseases
Disease References
Hawkinsinuria
  1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022313
KNApSAcK IDNot Available
Chemspider ID17216021
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5865
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID88508
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceUngnade, Herbert E.; Morriss, Francis V. Hydrogenation of phenolic acids. Journal of the American Chemical Society (1948), 70 1898-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Niederwieser A, Wadman SK, Danks DM: Excretion of cis- and trans-4-hydroxycyclohexylacetic acid in addition to hawkinsin in a family with a postulated defect of 4-hydroxyphenylpyruvate dioxygenase. Clin Chim Acta. 1978 Dec 1;90(2):195-200. [PubMed:719903 ]
  2. Hocart CH, Halpern B, Hick LA, Wong CO: Hawkinsinuria--identification of quinolacetic acid and pyroglutamic acid during an acidotic phase. J Chromatogr. 1983 Jul 8;275(2):237-43. [PubMed:6619234 ]
  3. Niederwieser A, Matasovic A, Neuheiser F, Wetzel E: New tyrosine metabolites in humans: hawkinsin and cis- and trans-4-hydroxycyclohexylacetic acids. Unusual adsorption of deuterated and non-deuterated hawkinsin during gas chromatography. J Chromatogr. 1978 Sep 1;146(2):207-12. [PubMed:701419 ]